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MedKoo Cat#: 596390 | Name: Mevinolinic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mevinolinic acid is an active metabolite of Lovastatin. Lovastatin is a HMG-CoA reductase inhibitor isolated from cultures of Aspergillus terreus. HMG-CoA reductase plays a role in cholesterol biosynthesis.

Chemical Structure

Mevinolinic acid
Mevinolinic acid
CAS#75225-51-3

Theoretical Analysis

MedKoo Cat#: 596390

Name: Mevinolinic acid

CAS#: 75225-51-3

Chemical Formula: C24H38O6

Exact Mass: 422.2668

Molecular Weight: 422.56

Elemental Analysis: C, 68.22; H, 9.06; O, 22.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
L 154819; Lovastatin acid; Lovastatin hydroxy acid; Mevinolinic acid; MK 819; Monacolin K acid; Monacolinic K acid; MSD 803 acid; MSD 803 free acid
IUPAC/Chemical Name
(3R,5R)-7-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoic acid
InChi Key
QLJODMDSTUBWDW-BXMDZJJMSA-N
InChi Code
InChI=1S/C24H38O6/c1-5-15(3)24(29)30-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-18(25)12-19(26)13-22(27)28/h6-7,10,14-16,18-21,23,25-26H,5,8-9,11-13H2,1-4H3,(H,27,28)/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
SMILES Code
C(C[C@H](C[C@H](CC(O)=O)O)O)[C@@H]1[C@]2([C@@H](OC([C@H](CC)C)=O)C[C@@H](C)C=C2C=C[C@@H]1C)[H]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 422.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Boruta T, Bizukojc M. Induction of secondary metabolism of Aspergillus terreus ATCC 20542 in the batch bioreactor cultures. Appl Microbiol Biotechnol. 2016 Apr;100(7):3009-22. doi: 10.1007/s00253-015-7157-1. Epub 2015 Nov 25. PubMed PMID: 26603760; PubMed Central PMCID: PMC4786612. 2: Boruta T, Bizukojc M. Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2014 Apr 10;175:53-62. doi: 10.1016/j.jbiotec.2014.01.038. Epub 2014 Feb 15. PubMed PMID: 24534845. 3: Bizukojc M, Pawlak M, Boruta T, Gonciarz J. Effect of pH on biosynthesis of lovastatin and other secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2012 Dec 31;162(2-3):253-61. doi: 10.1016/j.jbiotec.2012.09.007. Epub 2012 Sep 17. PubMed PMID: 22995742. 4: Bizukojc M, Ledakowicz S. Simultaneous biosynthesis of (+)-geodin by a lovastatin-producing fungus Aspergillus terreus. J Biotechnol. 2007 Dec 1;132(4):453-60. Epub 2007 Jul 10. PubMed PMID: 17689800. 5: Bizukojc M, Pawlowska B, Ledakowicz S. Supplementation of the cultivation media with B-group vitamins enhances lovastatin biosynthesis by Aspergillus terreus. J Biotechnol. 2007 Jan 1;127(2):258-68. Epub 2006 Jun 30. PubMed PMID: 16887228. 6: Baranova NA, Kreĭer VG, Egorov NS. [Concentration on Diapak C 16 capsules of lovastatin, mevinolinic acid and other inhibitors of biosynthesis of sterins produced by Penicillium citrinum 89]. Antibiot Khimioter. 2002;47(4):3-6. Russian. PubMed PMID: 12369143. 7: Carrascal M, Schneider K, Calaf RE, van Leeuwen S, Canosa D, Gelpí E, Abian J. Quantitative electrospray LC-MS and LC-MS/MS in biomedicine. J Pharm Biomed Anal. 1998 Sep 1;17(6-7):1129-38. PubMed PMID: 9884202. 8: Calaf RE, Carrascal M, Gelpí E, Abian J. Quantitative analysis of mevinolinic acid in human plasma by high-performance liquid chromatography coupled with negative-ion electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 1997;11(1):75-80. PubMed PMID: 9050262. 9: Baranova NA, Krĕier VG, Egorov NS. [Action of lovastatin--an inhibitor of cholesterol biosynthesis on bacterial bioluminescence]. Antibiot Khimioter. 1995 Aug;40(8):12-6. Russian. PubMed PMID: 8713431. 10: Vlahcevic ZR, Pandak WM, Hylemon PB, Heuman DM. Role of newly synthesized cholesterol or its metabolites on the regulation of bile acid biosynthesis after short-term biliary diversion in the rat. Hepatology. 1993 Sep;18(3):660-8. PubMed PMID: 8359807. 11: Kloss MW, Patrick DH, MacDonald JS. Studies on the effects of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors on the rodent forestomach. Food Chem Toxicol. 1991 Sep;29(9):621-8. PubMed PMID: 1937293. 12: Singer II, Kawka DW, Scott S, Bailey P, Kloss MW, Majka J, MacDonald JS. Inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase induce reductase accumulation and altered lamellar bodies in rat forestomach keratinocytes. Arterioscler Thromb. 1991 Sep-Oct;11(5):1156-65. PubMed PMID: 1911702. 13: Pandak WM, Vlahcevic ZR, Heuman DM, Hylemon PB. Regulation of bile acid synthesis. V. Inhibition of conversion of 7-dehydrocholesterol to cholesterol is associated with down-regulation of cholesterol 7 alpha-hydroxylase activity and inhibition of bile acid synthesis. J Lipid Res. 1990 Dec;31(12):2149-58. PubMed PMID: 1708805. 14: Pandak WM, Heuman DM, Hylemon PB, Vlahcevic ZR. Regulation of bile acid synthesis. IV. Interrelationship between cholesterol and bile acid biosynthesis pathways. J Lipid Res. 1990 Jan;31(1):79-90. PubMed PMID: 2313206. 15: Wang-Iverson D, Ivashkiv E, Jemal M, Cohen AI. Determination of lovastatin acid in serum by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 1989 May;3(5):132-4. PubMed PMID: 2520234. 16: Clarke DO, Brown NA. Valproic acid teratogenesis and embryonic lipid metabolism. Arch Toxicol Suppl. 1987;11:143-7. PubMed PMID: 3115231. 17: Stubbs RJ, Schwartz M, Bayne WF. Determination of mevinolin and mevinolinic acid in plasma and bile by reversed-phase high-performance liquid chromatography. J Chromatogr. 1986 Dec 19;383(2):438-43. PubMed PMID: 3644824. 18: Greenspan MD, Yudkovitz JB. Mevinolinic acid biosynthesis by Aspergillus terreus and its relationship to fatty acid biosynthesis. J Bacteriol. 1985 May;162(2):704-7. PubMed PMID: 3988710; PubMed Central PMCID: PMC218907. 19: Minsker DH, MacDonald JS, Robertson RT, Bokelman DL. Mevalonate supplementation in pregnant rats suppresses the teratogenicity of mevinolinic acid, an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme a reductase. Teratology. 1983 Dec;28(3):449-56. PubMed PMID: 6665743. 20: Demain AL. A new era of exploitation of microbial metabolites. Biochem Soc Symp. 1983;48:117-32. Review. PubMed PMID: 6400479.